Direct C-H Cyanation by ICN Formed In Situ: Nannozinone B

A novel method for C-H cyanation of different pyrans, pyrroles, indoles, and acyclic nucleophilic double bonds using TMSCN, NIS, and Zn(OTf)2 as a catalyst is described. The transformation is conducted under mild conditions tolerating a variety of functional groups. Zn(OTf)2 is likely to serve a dual catalytic role as an activator for TMSCN and for the cyanogen iodide generated in situ. Optimization, the substrate scope, and mechanistic observations are reported. Furthermore, this method is applied in the first total synthesis of the natural product nannozinone B.

Automated summary

A novel method for C-H cyanation of different pyrans, pyrroles, indoles, and acyclic nucleophilic double bonds using TMSCN, NIS, and Zn(OTf)2 as a catalyst is described. The transformation is conducted under mild conditions tolerating a variety of functional groups. Zn(OTf)2 is likely to serve a dual catalytic role as an activator for TMSCN and for the cyanogen iodide generated in situ. Optimization, the substrate scope, and mechanistic observations are reported. Furthermore, this method is applied in the first total synthesis of the natural product nannozinone B.